Manufacture of vat dyestuffs.



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atnnurno rnan or van nrnsrnrirs.

1 144 5 3? o Specification of Letters Patent.

No Drawin Patent Number 207097 it has been shown that indigoid vat dyestuffs can be obtained by condensing the reactive isatin-alpha derivatives with substituted phenols containing a free ortho-position.

Now, we have found that valuable vat dyestuffs differing from the known coloring matters by dyeing a much darker blue to violet-black or: deep black shades, may be obtained, if instead of the phenols used in the process of German Patent 207097, other derivatives or amino ,naphthols are employed which contain an amino group substituted in a suitable manner, 6. 57., by an acidyl or aminocarbonyl radical or residue, or in which the imino group forms a part of a closed nucleus, as for instance that of the naphthimidazole ring.

In lieu of the derivatives of amino-oXynaphthalenes above mentioned their substitution products, homologues and analogues may be employed in the same manner as well as the substitution products, homologues and analogues of the isatin-alpha derivatives.

The novel products of the present invention when made from isatin-alpha-anilid, for example, and derivatives of "2-a-mino-5- naphthol in which the amino group is substituted by a carbonyl-containing residue, have a constitution represented graphically by the following formula:

where X is a carbonyl-containing residue.

Example 1: 2.6 parts of .Z-benzoylamino I Application filed October 29, 1913. Serial Trio. Wit 3&3.

of the coloring matter is complete. After cooling the dyestuff obtained is filtered,

washed with alcohol and dried. It dyes textile fibers from the vat fast bluish-black shades. It 'has a constitution represented graphically by the following formula:

If in the foregoing example 1.? parts 01 5.5 dioXy -22 dinaphthyl urea are employed instead of the arts of Q-benzoylamino-5-oxynaphthalene, a bluish-black vat dyestufi' is also obtained.

Example 2: 6 parts of 5-chlorisatin-2.- para-chloranilid and parts of 5-oxy-1- phenyl-naphthylamin are heated with 30 parts of acetic anhydrid until the formation of the coloring matter is complete. After cooling the mass is filtered and washed with alcohol. lhe dyestuff obtained. is in a dry state a dark blue powder soluble in concentrated sulfuric acid with a clear blue color. When treated with alkaline reducing agents it forms a yellow vat from which wool is dyed brownish-black shades.

Instead of the 5-oXy-l-phenyl-naphthylamin equivalent quantities of S-oxy-l-anthraq'uinonyl-naphthylamin ,may be employed or equivalent parts of anthraquinonyl 1,2- triazole 5 oxynaphthalene ol tained from diazotized alpha-aininonnthraquinone, coupling with Q-amino-naphthalene, oxidizing to the triazole compound and fusion with alkali).

Example 3: parts of -oxy-u-phenyh 1.2-naphthimidazole and parts of isatinalpha anilid are heated together with 25 parts of acetic anhydrid until the condensation is finished. After cooling the dyestufl' is filtered, washed withacetic acid and alcohol and dried. The resulting coloring matter forms a bronze-like black powder soluble in sulfuric acid with a dark blue color.

When treated with reducing" agents the dyestutl forms yellow vat from which wool is dyed fast black shades.

We claim: 1. Process for producing dark him to violet to black dyestui'l's which i condensing isatin alpha derivatives with derivatives of amino-naphthols.

2. Process for producing dark blue to vio let to black dyestuffs which consists in condensing isatin-alpha derivatives with derivatives of amino-naphthols in which the amino group is substituted by an acidyl group.

3. Process for producing dark blue to violet to black dyestuffs which consists in condensing the isatin-alpha derivatives with derivatives of aminomaphthols in which the amino group is substituted by a carbonylcontaining residue.

l. As new products the vat dyestuifs being condensation products of isatin-alphaderivatives with derivatives of amino-naphthols, forming in a dry state dark blue to violet to black powders being transformed by alkaline reducing agents into their leuco compounds from which the coloring matters are regenerated on treatment with. oxidizing agents.

' 5. As new products the vat dyestuffs being'condensation products of isatin-alpha derivatives with derivatives of aminonaph thols in which the amino group is substituted by a carbonyl-containing residue, forming in a dry state dark blue to violet to black powders being transformed by alkaline reducing agents into their leuco compounds from which the coloringmatters are regenerated on treatment with oxidizing agents. i

6. As new products the vat dyestufis'being condensation products of isatin-alpha derivatives with derivatives of amino-naphthols in which the amino group is substituted byan acidyl-containing residue, forming in a dry state dark blue to violet to black powders being transformed by alkaline reducing agents into their leuco compounds from which the coloring matters are regenerated on treatment with oxidizing agents.

dry state dark blue to black powders, being 7. As new products the vat dyestuffs of the following formula:

where X is a carbonyl-containing residue, obtainable by condensing isatin-alpha-anilid with derivatives of 2-an1ino-5-naphthol in whichthe amino group is substituted by a carbonyl-containing residue, forming in a transformed by alkaline reducing agents into their leuco compounds from which the coloring matters are regenerated on treat ment with oxidizing agents.

8. As a new product the vat dyestutl of the following formula: 

